You Can Buy a Reel-to-Reel Tape of a Young Bob Dylan Performing Six Songs at the Gaslight Cafe

In September 1961, a 20-year-old folk singer named Bob Dylan had no apartment and no record deal. He was, more or less, a complete unknown.

One fateful gig at the Gaslight Cafe in Greenwich Village changed all that. Only about 20 people sat in the audience, but one of them—Dylan’s first manager, Terri Thal—had a boxy Ampex reel-to-reel recording device with her, according to the New York Times’ Colin Moynihan.

The six songs that Thal preserved would make all the difference in Dylan’s early career, earning him bigger gigs and contributing to his first record deal in October 1961.

Billed as “Bob Dylan’s first demo tape,” the reel-to-reel recording is now up for sale at RR Auction. It’s one of 85 Dylan or Dylan-adjacent lots, and it’s expected to sell for at least $20,000, according to Artnet’s Brian Boucher.

“When I was part of the folk music world, I never really thought about the future,” says Thal in a promotional video for the auction. “It never occurred to me that anything we had was important.”

“But looking back,” she says with astonishment, “I made the first tape of Dylan as a would-be folk singer.”

Bob Dylan’s First Demo Tape – Original Master Recording Hits the Auction Block

Not long after Dylan arrived in New York in January 1961, Thal met the young musician through her husband, Dave Van Ronk, a folk singer Dylan revered.

“He hung around our house a lot. He didn’t have a permanent place to live, and he slept on people’s couches, including ours,” Thal says in the video.

At that time, she was managing Van Ronk’s musical career, helping him get gigs “in places like Boston and Philly … even as far away as St. Louis at a folk club called Laughing Buddha,” as Dylan wrote in his 2004 memoir, Chronicles: Volume One.

“For me, those gigs were out of the question,” he continued. “You needed at least one record out even if it was on a small label to get work in any of those clubs.”

One day, he came to Thal for help. “I said, ‘Well, are you asking me to be your manager?’” Thal recalls asking Dylan. The answer was yes.

As Dylan’s first and only manager before he came under the wing of the influential Albert Grossman, Thal brought the young singer to the Gaslight Cafe and set up a recorder. To book shows outside of New York City, she explains, “I needed a way to show people what he sounded like.”

The six songs on the tape include “Old Man,” “He Was a Friend of Mine,” “Talkin’ Bear Mountain Picnic Massacre Blues,” “Song to Woody,” “Pretty Polly” and “Car, Car.” (A rough sketch of “Mr. Tambourine Man” also appears, but it was not recorded at the Gaslight and was added to the tape after Dylan signed with Grossman.)

Although the first four songs are Dylan compositions, early listeners were not impressed by Dylan’s originality.

When Thal played the tape to the owner of Club 47 in Cambridge, Massachusetts, he laughed and told her, “I can hire [Ramblin’] Jack Elliott. Why should I hire Bob Dylan?” Thal recalls in the video.

As Mark Davidson, the senior director of archives and exhibitions at the Bob Dylan Center in Tulsa, tells the Times, Dylan was “still sort of in that Woody Guthrie jukebox phase.”

On “Car, Car,” for instance, Van Ronk joins Dylan on stage to make car sounds in a playful cover of a Guthrie children’s tune.

These covers may not have been especially appealing to club promoters in the midst of the folk revival of the 1960s, but for today’s audiences, “this tape is a revelation—a rare look into Bob Dylan before he was a household name,” Bobby Livingston, executive vice president at RR Auction, tells Talker’s Dean Murray.

Bob Dylan – 6th September, 1961. Gaslight Café, New York

Eventually, the tape earned Dylan gigs in New Jersey and Long Island. But most importantly, it got him a spot at Gerde’s Folk City in Greenwich Village.

A Times article from September 29, 1961, lauded Dylan’s show at Gerde’s. “Mr. Dylan’s highly personalized approach toward folk song is still evolving. He has been sopping up influences like a sponge,” wrote Robert Shelton, a music critic who was later credited with helping launch Dylan’s career.

Shelton also hinted at some rough patches in Dylan’s performance style. But the criticism paled in comparison to the praise.

The gig at Gerde’s was a “tremendous success,” Thal says—one enabled by her recording of Dylan earlier that month. By late October, he had a record deal at Columbia. Things moved fast after that—and haven’t ceased since. Thal calls the tape the “first artifact in a long, prestigious and important musical career.”

As Shelton wrote in his 1961 review, “Mr. Dylan is vague about his antecedents and birthplace, but it matters less where he has been than where he is going, and that would seem to be straight up.”